Triethylamine → 4-[(2-Sulfamoyl-5-thienyl)sulfonyl]phenyl 1-acetylpiperidine-4-carboxylate

HRID 1632742Notes

Reaction equation

HRID 1632742 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[S:15][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[C:28]([N:31]1[CH2:36][CH2:35][CH:34]([C:37](Cl)=[O:38])[CH2:33][CH2:32]1)(=[O:30])[CH3:29]>CC(C)=O>[C:28]([N:31]1[CH2:32][CH2:33][CH:34]([C:37]([O:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([C:11]3[S:15][C:14]([S:16](=[O:17])(=[O:18])[NH2:19])=[CH:13][CH:12]=3)(=[O:9])=[O:10])=[CH:4][CH:3]=2)=[O:38])[CH2:35][CH2:36]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 8471Triethylamine3×HCID 127368925-(4-Hydroxyphenyl)sulfonylthiophene-2-sulfonamideHCID 534308101-Acetylpiperidine-4-carbonyl chloride hydrochloride2×

Product 1

HCID 204423674-[(2-Sulfamoyl-5-thienyl)sulfonyl]phenyl 1-acetylpiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-[(4-hydroxyphenyl)sulfonyl]thiophene-2-sulfonamide (3.19 g; 0.01 mole) in acetone (60 ml) at -15° was treated with triethylamine (1.11 g; 0.011 mole). Then 1-acetylpiperidine-4-carbonyl chloride hydrochloride (2.41 g; 0.011 mole) was added, portionwise, during 15 minutes at -15°. The cooling bath was removed and stirring was continued. After 20 hours at room temperature, the reaction mixture was treated with triethylamine (1.11 g; 0.011 mole). Then after stirring one hour longer, the reaction mixture was treated with 1-acetylpiperidine-4-carbonyl chloride hydrochloride (2.41 g; 0.011 mole) and triethylamine (2.22 g; 0.022 mole) and stirred at room temperature.

Workup

  1. customThe cooling bath was removed
  2. waitAfter 20 hours at room temperature
  3. stirringThen after stirring one hour longer
  4. stirringstirred at room temperature

Sources & evidence

ORD record
ord-d259bbaad2a743b2b218fca536653630
Source dataset
uspto-grants-1984_10
Patent number
US04477466

Reaction notes

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